Full orthogonality between Dde and Fmoc:: The direct synthesis of PNA-peptide conjugates

被引：102

作者：

Díaz-Mochón, JJ ^{[1
]}

Bialy, L ^{[1
]}

Bradley, M ^{[1
]}

机构：

[1] Univ Southampton, Sch Chem, Southampton SO17 1BJ, Hants, England

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 07期

关键词：

D O I：

10.1021/ol049905y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New deprotection conditions for the Dde amine protecting group that are fully orthogonal to Fmoc are described and successfully applied to the dual synthesis of PNA-peptide conjugates.

引用

页码：1127 / 1129

页数：3

共 19 条

[1] KINETICS AND MECHANISM OF REACTION OF HYDROXYLAMINE WITH CYTOSINE AND ITS DERIVATIVES [J].

BLACKBURN, GM ;

JARVIS, S ;

RYDER, MC ;

SOLAN, V .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (04) :370-375

[2] A peptide nucleic acid-nuclear localization signal fusion that mediates nuclear transport of DNA [J].

Brandén, LJ ;

Mohamed, AJ ;

Smith, CIE .

NATURE BIOTECHNOLOGY, 1999, 17 (08) :784-787

[3] Synthesis of polyamide nucleic acids (PNAs) using a novel Fmoc/Mmt protecting-group combination [J].

Breipohl, G ;

Knolle, J ;

Langner, D ;

OMalley, G ;

Uhlmann, E .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (06) :665-670

[4] A NOVEL LYSINE-PROTECTING PROCEDURE FOR CONTINUOUS-FLOW SOLID-PHASE SYNTHESIS OF BRANCHED PEPTIDES [J].

BYCROFT, BW ;

CHAN, WC ;

CHHABRA, SR ;

HONE, ND .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (09) :778-779

[5] Effects in live cells of a c-myc anti-gene PNA linked to a nuclear localization signal [J].

Cutrona, G ;

Carpaneto, EM ;

Ulivi, M ;

Roncella, S ;

Landt, O ;

Ferrarini, M ;

Boffa, LC .

NATURE BIOTECHNOLOGY, 2000, 18 (03) :300-303

[6]

HEIMER EP, 1984, INT J PEPT PROT RES, V23, P203

[7] Signal peptide mimics conjugated to peptide nucleic acid: A promising solution for improving cell membrane permeability [J].

Li, XX ;

Zhang, LR ;

Lu, JF ;

Chen, YZ ;

Min, JM ;

Zhang, LH .

BIOCONJUGATE CHEMISTRY, 2003, 14 (01) :153-157

[8] Synthesis of protein-nucleic acid conjugates by expressed protein ligation [J].

Lovrinovic, M ;

Seidel, R ;

Wacker, R ;

Schroeder, H ;

Seitz, O ;

Engelhard, M ;

Goody, RS ;

Niemeyer, CM .

CHEMICAL COMMUNICATIONS, 2003, (07) :822-823

[9] SEQUENCE-SELECTIVE RECOGNITION OF DNA BY STRAND DISPLACEMENT WITH A THYMINE-SUBSTITUTED POLYAMIDE [J].

NIELSEN, PE ;

EGHOLM, M ;

BERG, RH ;

BUCHARDT, O .

SCIENCE, 1991, 254 (5037) :1497-1500

[10] Peptide nucleic acid: a versatile tool in genetic diagnostics and molecular biology [J].

Nielsen, PE .

CURRENT OPINION IN BIOTECHNOLOGY, 2001, 12 (01) :16-20

← 1 2 →